Biologically Important Schiff Bases and Their Transition Metal Complexes
DOI:
https://doi.org/10.12723/mjs.21.5Keywords:
Transition metals, amino acids, Schiff bases, antimicrobial activity, DNA cleavageAbstract
Transition metal complexes with different ligand systems have been developed. Majority of them are derived from heteroaromatic cycles and Schiff bases of variety of aromatic aldehydes, diketones with amino acids, polyamines, N-aromatic cycles and ethylenediamines. Metal complexes of Schiff bases are used as polymers, dyes and in various biological systems. They show antimicrobial activity and can be used as suitable drug to treat bacterial and fungal infections. Most of the Cu, Ni and Co complexes are also capable of binding and cleaving DNA.
References
Bertini,gray,lippard,valentine, Bioinorganic Chemistry, Viva Books Pvt . ltd, Revised Ed:2007.
Fehmi N et al.,”Sulphur bonded Palladium (II) and Platinum (II) complexes of Biologically potent Thioamides,” Phosphorus, Sulphur, Silicon and the Related Elements,” T&F Online, vol.128 (1),pp.1-9, 1998.
E.H.R.Tomi et al., “Synthesis and Characterization of New Amino Acid-Schiff Bases and Studies their Effects on the Activity of ACP, PAP and NPA Enzymes (In Vitro)” E.J.Chem., vol. 9(2), pp.962-969, 2012.
Q.Zhang et al., “Schiff base transition metal complexes as novel inhibitors of xanthine oxidase”. E.Pub, vol.43 (4), pp.862-871, 2007.
Dharmaraj.N, “Ruthenium (II) complexes containing bidentate Schiff bases and their antifungal activity,” Trans.Met.Chem., Vol.26, pp.105-109, 2001.
Farrell.N, “Recent developments in the chemistry of, 1,3,2-diazaborolines-(2,3-dihydro-1H-1,3 diazaboroles,” Coord. Chem. Rev., vol.232 (1–2), pp.1–31, 2007.
M.D.Pandey et al., “Synthetic, Spectral, Structural and Antimicrobial Studies of Some Schiff Bases 3-d Metal Complexes,” Rus.J.Inorg.Chem., vol.56, no.11, pp.1757–1764, 2011.
B. Selvakumar et al., “Structures, Spectra, and DNA Binding Properties of Mixed Ligand Copper(II) Complexes of Iminodiacetic Acid: The Novel Role of Diimine Conformation and Co-ligands on DNA Hydrolytic and Oxidative Double Strand DNA Cleavage Certain Diiminies and Iminodiacetic Acid Bound to Calf Thymus DNA,” J. Inorg. Biochem., Vol.100, pp.316-321, 2006.
Bringmann G., “The total synthesis of streptonigrin and related antitumor antibiotic natural products”. Tetrahedron, vol.60 (16), pp.3539-3574, 2004.
O’Neill et al., “4-aminoquinolines-past, present and future: a chemical perspective”. Pharmacology & Therapeutics, vol.1, pp.77-82, 1998.
Foley M et al., “Quinoline antimalarials: mechanisms of action and resistance and prospects for new agents”. Pharmacology & Therapeutics,” vol.79 (1), pp.55-87, 1998.
Basavaraju et al., “Transition metal complexes of Quinoline [3, 2-b]benzodiazepine and quinoline [3,2-b]benzoxazepine: Synthesis, Characterisation and Antimicrobial studies”. Bioinorg.Chem&Appl., Sept 2007 Vol.2007, Article ID 42587, 6 pages.
G. Bouet et al., “Synthesis, characterization and antifungal activity of a series of Cobalt(II) and Nickel(II) complexes with ligands derived from reduced N, N’-o-Phenylenebis(Salicylideneimine),” Transt.Met.Chem., vol.33, pp.511-516, 2003.
Tudor Rosu, et. al., “Synthesis and characterization of some new complexes of Cu(II), Ni (II) and V(IV) with Schiff base derived from indole-3-carboxaldehyde. Biological activity on prokaryotes and eukaryotes,” Eur.J.Med.Chem., vol.53, pp.380-389, 2012.
Kulkarni et al., “Electrochemical properties of some Transition metal complexes: Synthesis, Characterization and In-vitro antimicrobial studies of Co(II), Ni(II), Cu(II), Mn(II) and Fe(III) Complexes,” Int. J. Electrochem. Sci., vol.4, pp.717-729, 2009.
N.Raman et al., “Comparison of the Cleavage Ability of Metal Complexes Containing Tetradentate Schiff Bases,” Rus.J.Inorg Chem., Vol. 53, No. 2, pp. 213–219 2008.
N.Raman et al., “Design, Synthesis, Spectroscopic Characterization, Biological Screening, and DNA Nuclease Activity of Transition Metal Complexes Derived from a Tridentate Schiff Base,” Rus.J.Coord.Chem., Vol. 34, No. 6, pp. 400–406, 2008.
N.Raman et al., “Molecular Designing, Structural Elucidation, and Comparison of the Cleavage Ability of Oxovanadium(IV) Schiff Base Complexes,” Rus.J.Coord.Chem., Vol. 33, No. 1, pp. 7–11, 2007.
J.Joseph et al., “Synthesis, characterization and antimicrobial activities of copper complexes derived from 4-aminoantipyrine derivatives,” J. Saud. Chem. Soc, April 2011, doi:10.1016/ j.jscs.2011.04.007
K. R. Grunwald et al., “Pyridazine-Based Ligands and Their Coordinating Ability towards First-Row Transition Metals,” Eur. J. Inorg. Chem, vol.15, pp.2297-2305, 2010.
Deligönül.N et al., “Synthesis and Characterization, Catalytic, Electrochemical and Thermal Properties of Tetradentade Schiff Base Complexes,” Trans. Met. Chem. vol.31, pp.920-929, 2006.
V.B.Badwaik et al., “Transition metal complexes of a Schiff base: synthesis, characterization, and antibacterial studies,”
J. Coord. Chem., vol.62, no.12, pp.2037-2047, 2009.
K.B.Gudasi et al., “X-ray Crystal Structure of the N-(2-hydroxy-1-naphthalidene) phenylglycine Schiff Base. Synthesis and Characterization of its Transition Metal Complexes,” Trans. Met. Chem., vol.31 no.5, pp.580-585, 2012.
L. Li et al., “A copper (II) complex of the Schiff base from L-valine and 2-hydroxy-1-naphthalidene plus 1, 10-phenanthroline: synthesis, crystal structure, and DNA interaction,” Trans. Met. Chem., vol.37, pp.175–182 2012.
Y.Matsuo et al., “Formation of Schiff Bases of Pyridoxal Phosphate. Reaction with Metal Ions,” J. Am. Chem. Soc., vol.79 no.8, pp. 2011–2015, 1957.
G.S.Kurdekar et al., “Synthesis, characterization, antibiogram and DNA binding studies of novel Co(II),Ni(II), Cu(II) and Zn (II) complexes of Schiff base ligands with quinoline core,” Med. Chem. Res., vol.20, pp.421-429, 2011.
B. K. Singh et al., “Synthesis characterization and biological activity of transition metal complexeswith Schiff bases derived from 2-nitrobenzaldehydewith glycine and methionine,” Spectrochim. Acta Part A, vol.94, pp.143– 151, 2012.
Pandeya et al., “indole, a versatile nucleus in pharmaceutical field”Int.J.Curr.Pharma.Res., vol.1, no.5, pp.1-17, 2010.
A.K.Mishra, “Synthesis, characterization and biological activity of Schiff base analogues of indole-3-carboxaldehyde,” Eur. J. Inorg. Chem., vol.43, pp.160-165, 2008.
M.S.Nair et al., “Synthesis, characterization and biological studies of some Co(II), Ni(II) and Cu(II) complexes derived from indole-3-carboxaldehyde and glycylglycine as Schiff base ligand,” Arab.J.Chem., vol.3, pp.195–204, 2010.
B.U Nair et al., “Oxidative DNA cleavage mediated by a new copper (II) terpyridine complex: Crystal structure and DNA binding studies,” J.Inorg.Biochem., vol.12, pp.2299-2307, 2005.
Y.M.Liu et al., “DNA Binding and cleavage activity of Ni(II) complex with all-trans retinoic acid,” J.Inorg.Biochem., vol. 100, no. 10, pp. 1685–1691, 2006.
Lippard et al.,”New metal complexes as potential therapeutics,” Curr. Opin. Chem. Biol., vol.7 no.4, pp.481-489, 2003.
P. Sharma et al, “Coordination Modes of a Schiff Base Pentadentate Derivative of 4-Aminoantipyrine with Cobalt (II), Nickel(II) and Copper(II) Metal Ions: Synthesis, Spectroscopic and Antimicrobial study,” Molecules, vol.14, pp.174-190, 2009.
B.U.Nair et al., “Interaction of DNA with [Cr(Schiff base)(H2O)2]ClO4,” J.Photochem.Photobiol B: Biology, vol.86, pp.272–278, 2007.
S.M.Zingde et al., “Carbohydrate-conjugate heterobimetallic complexes: synthesis, DNA binding studies, artificial nuclease activity and in vitro cytotoxicity,” Carbohydrate Research, vol.346, pp.2886–2895, 2011.
K.Abdi et al, “Mononuclear copper(II) complex with terpyridine and an extended phenanthroline base, [Cu(tpy)(dppz)]2+: Synthesis, crystal structure, DNA binding and cytotoxicity,” Polyhedron, vol.31, pp.638–648 2012.
M.Palaniandavar et al., “DNA binding and cleavage properties of certain tetra ammine ruthenium (II) complexes of modified 1,10-phenanthrolines – effect of hydrogen-bonding on DNA-binding affinity,” J.Inorg.Biochem., vol.98 pp. 219–230, 2004.
D.Wang et al., “A ternary copper(II) complex for supramolecular assembly with double helices: synthesis, crystal structure, DNA-binding and DNA-cleavage properties,” Trans. Met. Chem., vol.36, pp.289–295, 2011.
R.Zeng et al., “Synthesis, characterization and DNA interaction of copper (II) complexes with Schiff base ligands derived from 2-pyridinecarboxaldehyde and polyamines,” Inorg.Chem. Commu., vol.13, pp.1421–1424, 2010.
N. Raman et al., “Probing the DNA-binding behavior of tryptophan incorporating mixed-ligand complexes” Monatsh chem., DOI: 10.1007/s00706-012-0718-4, 2012.
Z.Liu et al., “DNA-binding, antioxidant activity and solid-state fluorescence studies of copper(II), zinc(II) and nickel(II) complexes with a Schiff base derived from 2-oxo-quinoline-3-carbaldehyde,” Trans. Met. Chem., vol.36, pp.489–498, 2011.
A.K. Das, Bioinorganic chemistry, Books and Allied Pvt ltd, Revised Ed: 2008.
Ingo Ott, Ronald Gust, “Non Platinum Metal Complexes as Anti-cancer Drugs,” Archiv der Pharmazie, vol.340, no.3, 117-126, 2007.
P.J.Dyson et al., “Development of organometallic (organo-transition metal) pharmaceuticals,” App.Organomet.Chem, vol.19, no.1, pp.1–10, 2005.
A.K.Kondapi et al., “Inhibition of Topoisomerase II Catalytic Activity by Two Ruthenium Compounds: A Ligand-Dependent Mode of Action,” Biochemistry, vol.38, no.14, pp.4382–4388, 1999.
George Mokdsi, Margaret M., “Harding Inhibition of human topoisomerase II by the antitumor metallocenes,” J.Inorg. Biochem, vol.83, no.2–3, pp.205–209, 2001.
P.R.Chetana et al., “Synthesis, structure, DNA binding and oxidative cleavage activity of ternary (L-leucine/isoleucine) copper(II) complexes of heterocyclic bases,” Polyhedron, vol.27, pp.1343–1352, 2008.
J.D.Ranford et al., “Complexes of platinum(II) or palladium(II) with1,10-phenanthroline and amino acids,” Inorg.Chimi.Acta, vol.,.304, pp. 38–44, 2000.
P.Reddy et al, “Synthesis, structure, DNA binding and cleavage properties of ternary amino acid Schiff base-phen/bipy Cu(II) complexes,” J.InorgBiochem, vol.105, pp.1603–1612, 2011.
A. R. Chakravarty et al., “Photocleavage of DNA by copper(II) complexes,” Indian Academy of Sciences, J.Chem.Sci., vol.118, no.96, pp.443–453, 2006.
P.R.Chetana et al., “New ternary copper(II) complexes of L-alanine and heterocyclic bases: DNA binding and oxidative DNA cleavage activity,” Inorg.Chim.Acta, vol.362 pp.4692–4698, 2009.
S. Arunachalam et al., “DNA binding and antimicrobial studies of some polyethyleneimine-copper(II) complex samples containing1, 10-phenanthroline and L-theronine as co-ligands,” Polyhedron, vol.26, pp.3255–3262, 2007.
D. Wang et al., “Synthesis, Characterization, DNA-binding Properties and DNA Cleavage of a New Ternary Copper(II) Complex with Mixed-ligands of Tridentate Schiff Base and 1,10- Phenanthroline,” Chin. J.Chem. , Vol. 29, no. 2, pp. 259–266, 2011.
S. Arunachalam et al, “DNA binding and antimicrobial studies of polymer–copper(II) complexes containing 1,10-phenanthroline and L-phenylalanine ligands,” Eur. J.Med.Chemi., vol.44, pp.1878–1883, 2009.
P.R.Chetana et al., “DNA binding and oxidative cleavage activity of ternary(L-proline)copper(II) complexes of heterocyclic bases,” Polyhedron, vol.26, pp.5331–5338,2007.
A.R.Chakravarty et al., “Synthesis, crystal structure, DNA binding and photo-induced DNA cleavage activity of (S-methyl-L-cysteine) copper(II) complexes of heterocyclic bases,” J.Inorg.Biochem, vol.101, pp. 233–244, 2007.
A.R.Chakravarty et al., “Synthesis, crystal structures, DNA binding and cleavage activity of L-glutamine copper(II) complexes of heterocyclic bases,” Inorg.Chimi.Acta, vol.362, pp.1591–1599, 2009.
B.Satyanarayana et al., “Synthesis and DNA cleavage properties of ternary Cu(II) complexes containing histamine and amino acids,” Tetrahedron Letters, vol.47, pp.7311–7315, 2006.
D.S.Pandey et al., “Synthesis, and characterization of ruthenium(II) polypyridyl complexes containing -amino acids and its DNA binding behavior,” J.Organomet.Chem, vol.694, pp.3570–3579, 2009.
A.S.Gaballa et al., “Synthesis, characterization and biological activity of some platinum(II) complexes with Schiff bases derived from, , and phenylenediamine” Spectrochim. Acta Part A vol.67, pp.114–121, 2007.
Y.Huang et al, “Synthesis, characterization and DNA interaction of copper (II) complexes with Schiff base ligands derived from 2-pyridinecarboxaldehyde and polyamines,” Inorg.Chem.Commun., vol.13, pp.1421–1424, 2010
V.C.Silveira et al, “Double-strand DNA cleavage induced by oxindole-Schiff base copper(II) complexes with potential antitumor activity,” J.InorgBiochem, vol.102, pp.1090–1103, 2008.
M.Wang et al., “DNA-binding, antioxidant activity and solid-state fluorescence studies of copper(II), zinc(II) and nickel(II) complexes with a Schiff base derived from 2-quinoline-3-carbaldehyde,” Trans. Met. Chem, vol.36, pp.489–498, 2011.
S.Eldin et al, “Synthesis, spectral, antimicrobial and antitumor assessment of Schiff base derived from and its transition metal complexes,” Spectrochim.Acta Part A, vol.79, pp.1331– 1337, 2011.
Ahmed A. El-Sherif, Taha M. A Eldebss, “Synthesis, spectral characterization, solution equilibria, in vitro antibacterial and cytotoxic activities of Cu(II), Ni(II), Mn(II), Co(II) and Zn(II) complexes with Schiff base derived from 5-bromosalicylaldehyde and 2-aminomethylthiophene,” Spectrochim. Acta Part A, vol.79, pp.1803–1814, 2011.
M.S.Nair et al., “Synthesis, characterization and biological studies of Co(II),Ni(II), Cu(II) and Zn(II) complexes with with pyrral-L-histidinate,” Arab. J.Chem., vol.5, pp.179–186, 2012.
Daqi Wang, “Synthesis, crystal structure and DNA-binding properties of a new copper (II) complex with L-valine Schiff base and 1,10-phenanthroline,” J.Mol.Struc., vol.98, pp.57-63 2011.
Tao Xu et al., “Synthesis, crystal structure, and DNA interaction studies of a mixed-ligand copper(II) complex of 1,10-phenanthroline and a Schiff base derived from isoleucine Trans. Met.Chem, vol.36, pp.565–571, 2011.
S.Yan et al., “DNA binding and cleavage activity of reduced amino-acid Schiff base complexes of cobalt(II), copper(II), and cadmium(II),” Trans Met.Chem, vol.34, pp.475–481, 2009.
M.A.Neelakantan et al., “Spectral characterization, cyclic voltammetry, morphology, biological activities and DNA cleaving studies of amino acid Schiff base metal(II) complexes,” Spectrochim. Acta Part A, vol.71, pp.1599–1609, 2008.
B.Wang et al., “Spectra DNA-binding affinities of Copper(II), Nickel(II) complexes with a novel glycine Schiff base derived from chromone,” Spectrochim. Acta Part A, vol.68, pp.912–917 2007.
R.D. Gillard et al., “Preparation and characterisation of new oxovanadium (IV) Schiff base complexes derived from salicylaldehyde and simple dipeptides,” Inorg.Chim.Acta, vol.305, pp.7–13, 2000.
A.R.Chakravarty et al., “Iron(III) Schiff base complexes of arginine and lysine as netropsin mimics showing AT-selective DNA binding and photonuclease activity,” J.InorgBiochem, vol.104, pp.477–484, 2010.
A. R.Chakravarty et al., “Hydrolytic Cleavage of DNA by Ternary Amino Acid Schiff Base Copper(II) Complexes Having Planar Heterocyclic Ligands,” Eur.J.Inorg.Chem., vol.7, pp.1440–1446, 2004.
T. M. Das et al, “Structural and DNA cleavage of sugar-derived Schiff base ligands and their dinuclear Cu(II) complexes,” Carbohydrate research, vol.345, no.9, pp.1077–1083, 2010.
A.R.Chakravarty et al.,”Synthesis, crystal structure, and nuclease activity of planar mono-heterocyclic base copper(II) complexes,” J.InorgBiochem, vol.94, pp.171–178, 2003.
S. Satyanarayana et al., “DNA–interactions of ruthenium(II) & cobalt(III) phenanthroline and bipyridine complexes with a planar aromatic ligand 2-(2-fluronyl)1H-imidazole [4,5-f] 1,1Phenanthroline” J.Incl.Phenom.Macrocycl.Chem, vol.70, pp.187–195, 2011.
B. U. Nair et al., “Interaction of chromium(III) complex of chiral binaphthyl tetradentate ligand with DNA,” Bioorg. Med. Chem., vol.14, pp.3300–3306, 2006.
Published
Issue
Section
License
Copyright (c) 2012 Riya Datta, Ramya V
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.